#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:19:39 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292786 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/29/7132998.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7132998
loop_
_publ_author_name
'Das, Animesh'
'Maji, Biplab'
_publ_section_title
;
 Substrate-controlled divergent remote C-H and N-H polyfluoroarylation of
 2-aminopyrimidines with polyfluoroarenes via Pd(II)/Pd(0)
 catalysis.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5630
_journal_page_last               5633
_journal_paper_doi               10.1039/d4cc01518e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H10 F5 N3'
_chemical_formula_sum            'C17 H10 F5 N3'
_chemical_formula_weight         351.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-02
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-11-29 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.917(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4065(2)
_cell_length_b                   6.17670(10)
_cell_length_c                   17.7705(3)
_cell_measurement_reflns_used    12348
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      67.9590
_cell_measurement_theta_min      2.6370
_cell_volume                     1486.72(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    105.00 170.00   0.50    0.40    --   96.35  96.00-120.00  130
  2  ω    -29.00  31.00   0.50    0.20    --   40.58 -25.00-180.00  120
  3  ω    -25.00  43.00   0.50    0.20    --   40.58 -38.00-120.00  136
  4  ω    -35.00  24.00   0.50    0.20    --   40.58 -12.00-150.00  118
  5  ω    -35.00  24.00   0.50    0.20    --   40.58 -12.00  60.00  118
  6  ω    -25.00  51.00   0.50    0.20    --   40.58 -45.00   7.00  152
  7  ω     44.00 127.00   0.50    0.40    --   96.35-145.00-120.00  166
  8  ω     23.00 106.00   0.50    0.40    --   96.35 -96.00-150.00  166
  9  ω     18.00  78.00   0.50    0.20    --   40.58-104.00 -60.00  120
 10  ω     33.00 110.00   0.50    0.40    --   96.35-117.00  60.00  154
 11  ω     33.00 110.00   0.50    0.40    --   96.35-117.00  30.00  154
 12  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 -90.00   54
 13  ω     29.00  83.00   0.50    0.40    --   96.35 -68.00-120.00  108
 14  ω     29.00  83.00   0.50    0.40    --   96.35 -68.00-150.00  108
 15  ω     29.00  83.00   0.50    0.40    --   96.35 -68.00 -90.00  108
 16  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00   0.00   54
 17  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 -30.00   54
 18  ω     28.00  68.00   0.50    0.40    --   96.35 -59.00  30.00   80
 19  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00  60.00   54
 20  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00  90.00   54
 21  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 150.00   54
 22  ω     28.00 105.00   0.50    0.40    --   96.35 -77.00  60.00  154
 23  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 -60.00   54
 24  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00-120.00   54
 25  ω     70.00 165.00   0.50    0.40    --   96.35  77.00 -60.00  190
 26  ω     75.00 165.00   0.50    0.40    --   96.35  59.00-180.00  180
 27  ω     77.00 163.00   0.50    0.40    --   96.35  50.00-150.00  172
 28  ω     72.00 164.00   0.50    0.40    --   96.35  68.00-120.00  184
 29  ω     80.00 164.00   0.50    0.40    --   96.35  42.00 -60.00  168
 30  ω     80.00 164.00   0.50    0.40    --   96.35  42.00   0.00  168
 31  ω     77.00 163.00   0.50    0.40    --   96.35  50.00  30.00  172
 32  ω     77.00 163.00   0.50    0.40    --   96.35  50.00 120.00  172
 33  ω     81.00 167.00   0.50    0.40    --   96.35  25.00  90.00  172
 34  ω     79.00 164.00   0.50    0.40    --   96.35  45.00 157.00  170
 35  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 150.00  190
 36  ω     14.00 109.00   0.50    0.20    --   40.58  77.00  90.00  190
 37  ω     23.00 108.00   0.50    0.20    --   40.58  45.00 157.00  170
 38  ω     26.00 111.00   0.50    0.20    --   40.58  25.00  90.00  170
 39  ω     14.00 109.00   0.50    0.20    --   40.58  77.00  30.00  190
 40  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 -60.00  190
 41  ω     14.00 109.00   0.50    0.20    --   40.58  77.00-150.00  190
 42  ω    -31.00  30.00   0.50    0.20    --  -40.58  25.00-150.00  122
 43  ω    -47.00 -15.00   0.50    0.40    --  -82.50  42.00 -60.00   64
 44  ω    -47.00 -15.00   0.50    0.40    --  -82.50  42.00  30.00   64
 45  ω    -47.00 -15.00   0.50    0.40    --  -82.50  42.00 120.00   64
 46  ω    -51.00 -15.00   0.50    0.40    --  -82.50  45.00 157.00   72
 47  ω    -51.00  27.00   0.50    0.20    --  -40.58  45.00 157.00  156
 48  ω    -96.00 -19.00   0.50    0.20    --  -40.58 138.00 150.00  154
 49  ω    -80.00  -9.00   0.50    0.40    --  -82.50  96.00-150.00  142
 50  ω   -108.00 -23.00   0.50    0.20    --  -40.58 -45.00   7.00  170
 51  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -30.00  182
 52  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-150.00  190
 53  ω   -107.00 -25.00   0.50    0.20    --  -40.58 -38.00-180.00  164
 54  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -90.00  182
 55  ω   -150.00 -65.00   0.50    0.40    --  -82.50 -45.00   7.00  170
 56  ω   -151.00 -55.00   0.50    0.40    --  -82.50 -77.00 150.00  192
 57  ω   -151.00 -55.00   0.50    0.40    --  -82.50 -77.00  90.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0969309000
_diffrn_orient_matrix_UB_12      -0.0177311000
_diffrn_orient_matrix_UB_13      -0.0717738000
_diffrn_orient_matrix_UB_21      -0.0452650000
_diffrn_orient_matrix_UB_22      -0.1386702000
_diffrn_orient_matrix_UB_23      0.0507348000
_diffrn_orient_matrix_UB_31      -0.0386911000
_diffrn_orient_matrix_UB_32      0.2064927000
_diffrn_orient_matrix_UB_33      0.0279341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.141
_diffrn_reflns_theta_min         3.263
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0483P)²+0.6326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2482
_reflns_number_total             2708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01518e2.cif
_cod_data_source_block           adaaf115_auto
_cod_depositor_comments
'Adding full bibliography for 7132998--7132999.cif.'
_cod_database_code               7132998
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     '100 K'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.711
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C16(H16), C6(H6), C17(H17), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.914
_oxdiff_exptl_absorpt_empirical_full_min 0.528
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.81682(6) 0.71846(14) 0.47069(5) 0.0316(2) Uani 1 1 d . . . . .
F5 F 0.75150(6) 0.04359(14) 0.33918(5) 0.0322(2) Uani 1 1 d . . . . .
F4 F 0.91598(7) 0.08822(15) 0.29904(5) 0.0363(2) Uani 1 1 d . . . . .
F2 F 0.97921(6) 0.76429(15) 0.42887(5) 0.0358(2) Uani 1 1 d . . . . .
F3 F 1.02825(6) 0.44851(16) 0.34172(5) 0.0373(2) Uani 1 1 d . . . . .
N3 N 0.54125(8) 0.48277(19) 0.42392(6) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.61756(8) 0.60455(19) 0.33039(6) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.69475(8) 0.35427(19) 0.42807(6) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.70342(10) 0.2115(2) 0.49401(8) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.61383(9) 0.4863(2) 0.39276(7) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.53957(10) 0.7325(2) 0.29696(8) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.538684 0.819574 0.252660 0.029 Uiso 1 1 calc R . . . .
C5 C 0.64735(10) -0.0891(2) 0.55265(8) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.598746 -0.196224 0.549179 0.029 Uiso 1 1 calc R . . . .
C8 C 0.77948(9) 0.3806(2) 0.40547(8) 0.0221(3) Uani 1 1 d . . . . .
C16 C 0.46005(10) 0.7444(2) 0.32366(8) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.405216 0.836308 0.299006 0.030 Uiso 1 1 calc R . . . .
C9 C 0.83937(10) 0.5627(2) 0.42761(8) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.63424(10) 0.0513(2) 0.48888(8) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.577930 0.037602 0.441818 0.028 Uiso 1 1 calc R . . . .
C3 C 0.73059(10) -0.0760(2) 0.62183(8) 0.0252(3) Uani 1 1 d . . . . .
C17 C 0.46507(10) 0.6145(2) 0.38845(8) 0.0236(3) Uani 1 1 d . . . . .
H17 H 0.411972 0.619039 0.408677 0.028 Uiso 1 1 calc R . . . .
C13 C 0.80715(10) 0.2215(2) 0.36220(8) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.92266(10) 0.5868(2) 0.40661(8) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.89088(11) 0.2425(2) 0.34140(8) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.78553(10) 0.2298(3) 0.56289(8) 0.0284(3) Uani 1 1 d . . . . .
H1 H 0.832536 0.341237 0.567198 0.034 Uiso 1 1 calc R . . . .
C11 C 0.94819(10) 0.4260(3) 0.36336(8) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.79895(11) 0.0853(3) 0.62550(8) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.856225 0.097150 0.671897 0.037 Uiso 1 1 calc R . . . .
C4 C 0.74640(12) -0.2324(3) 0.69018(9) 0.0326(3) Uani 1 1 d . . . . .
H4A H 0.706027 -0.188496 0.722169 0.049 Uiso 1 1 calc GR . . . .
H4B H 0.816230 -0.232138 0.723892 0.049 Uiso 1 1 calc GR . . . .
H4C H 0.727218 -0.378348 0.668907 0.049 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N3 C14 115.19(11) . . ?
C15 N2 C14 115.11(11) . . ?
C14 N1 C7 123.80(11) . . ?
C14 N1 C8 118.47(11) . . ?
C8 N1 C7 117.20(10) . . ?
C6 C7 N1 121.59(12) . . ?
C6 C7 C1 119.65(13) . . ?
C1 C7 N1 118.71(12) . . ?
N3 C14 N2 127.30(12) . . ?
N3 C14 N1 117.27(11) . . ?
N2 C14 N1 115.44(11) . . ?
N2 C15 C16 123.25(12) . . ?
C6 C5 C3 121.31(13) . . ?
C9 C8 N1 121.60(12) . . ?
C13 C8 N1 120.86(12) . . ?
C13 C8 C9 117.52(12) . . ?
C15 C16 C17 116.07(13) . . ?
F1 C9 C8 119.72(12) . . ?
F1 C9 C10 118.70(13) . . ?
C10 C9 C8 121.58(13) . . ?
C7 C6 C5 119.86(12) . . ?
C5 C3 C4 121.39(13) . . ?
C2 C3 C5 117.77(13) . . ?
C2 C3 C4 120.84(13) . . ?
N3 C17 C16 123.08(12) . . ?
F5 C13 C8 119.70(12) . . ?
F5 C13 C12 118.76(12) . . ?
C12 C13 C8 121.55(13) . . ?
F2 C10 C9 120.30(13) . . ?
F2 C10 C11 120.10(12) . . ?
C11 C10 C9 119.60(13) . . ?
F4 C12 C13 120.74(13) . . ?
F4 C12 C11 119.63(12) . . ?
C11 C12 C13 119.62(13) . . ?
C7 C1 C2 119.93(13) . . ?
F3 C11 C10 120.23(13) . . ?
F3 C11 C12 119.64(13) . . ?
C12 C11 C10 120.13(13) . . ?
C3 C2 C1 121.45(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.3368(16) . ?
F5 C13 1.3394(16) . ?
F4 C12 1.3382(16) . ?
F2 C10 1.3425(16) . ?
F3 C11 1.3416(16) . ?
N3 C14 1.3396(17) . ?
N3 C17 1.3387(18) . ?
N2 C14 1.3438(17) . ?
N2 C15 1.3360(18) . ?
N1 C7 1.4376(17) . ?
N1 C14 1.3854(17) . ?
N1 C8 1.4184(16) . ?
C7 C6 1.3852(19) . ?
C7 C1 1.3871(19) . ?
C15 C16 1.3832(19) . ?
C5 C6 1.388(2) . ?
C5 C3 1.397(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.388(2) . ?
C16 C17 1.3850(19) . ?
C9 C10 1.381(2) . ?
C3 C2 1.387(2) . ?
C3 C4 1.5073(19) . ?
C13 C12 1.383(2) . ?
C10 C11 1.380(2) . ?
C12 C11 1.378(2) . ?
C1 C2 1.388(2) . ?
